Because I end up doing 90% of my sailing alone I need to be comfortable handling the boat without the benefit of crew.
I have a BeneteauOceanis 331 that is paid for and very well equipped.
Works for me.

As long as we're talking about LWL (waterline length), and non-surfing boats. Many "traditional" boats (like mine, sort of, although we have a short fin keel) have fairly long overhangs, where a more modern boat will have a longer waterline for the same length overall. With any decent wind, longer waterline almost always gives you faster average speed. Of course overhang has it's benefits: drier decks, easier anchor handling, and good looks (IMHO), to name a few.

If you're comparing a heavy full-keel boat to a lightweight surfing machine, the downwind performance will be like night and day. Please note that I'm not saying that the ultra-light boat would make a great cruiser, but actual boat performance covers a wide range.

Point taken. I wasn't accounting for surfing, which is the exception, anyway.

Okay, let's run those numbers to take a look at what the OP's dream boat would look like. He wants to be LOA 36-38, so lets assume a 32' waterline. To hit his DLR that boat will have to weight around 19,000 lbs. Now to get into his desired SA/D ratio, that boat would have to have exactly 1,000 square feet of sail area. (!)

Let's say you wanted to customize a Tayana 37 to create the OP's dream boat. You'd have to shave 5,000 pounds off the displacement, while at the same time you'd be more than doubling the sail area.

Anyone want to speculate how that puppy is gonna sail?

Now let's try it the other way. A Catalina 380 has pretty close to the OP's desired DLR at 248.92. But its SA/D is only 16.35, so to get it up to the OP's standards we're going to have to add several hundred square feet of sail area. (That's going to be a 30% increase in sail area, so you're not going to accomplish this just by adding a square-top main and a bit of roach.)

Again, anyone want to speculate on how that puppy is gonna sail? (Can you say "weather helm?" How about "Round up?") The Catalina 380 is certainly closer to the boat the OP wants, but the fact is that the OP's dream boat doesn't exist and never will, because those two ratios are not going to work together in the size boat the OP wants to find.